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WWAND
Sort of too late for this question as it's pretty much already done, or in the process of happening, but.....
Is 7 yrs old too little to send your kid off on a swimming playdate with a friends family? Because I totally did that today and I've been staring at my phone all day, having mini panic attack convinced he's going to drown. So far so good...
It not like I had a bad feeling about it...if I did, I wouldn't have sent him. I'm just being overly protective, which I always said I wasn't going to be 'THAT' kind of mom. 
Is 7 too little to send him on his own with them? Which brings up other points like at what age would I let him go there for the night? or things like that? I think 7 is too little to spend the night at a friends, considering he's never spent the night away from home EVER, not even with grandparents, without DH or I....
Re: WWAND
]Keep in mind I don't have a 7 year old...
Would I send them on a playdate to a crazy public pool? Probably not. Would I send them to someplace like Prarie Life where there's maybe 10 kids and a bunch of parents/nannies in the middle of the week? Yes. Especially if I was close with the parents.
As far as the slumber party, I'd start with a slumber party without you or DH. It would be good for everyone.
If it's a parent you know well and trust, I dont' think 7 is too young at all. If it's one parent and 10 boys...no effing way.
I would also say it's not too young for a sleepover. I might start with grandparents or someone he knows really well if he has never been away from you but no biggie, IMO.
love is for every her, love is for every him, love is for everyone
Ditto! You are breeding him to live in your basement until he's 30!
omg Shannon...you are going to be THAT MIL.
THIS!!
Just the mom, the two boys, and maybe his sisters? (who are in HS) It's not a public pool....well its at the JCC. So a membership pool?
As far as the sleepover things goes, I ask because I'm sure it will come up this year. It's not like won't let him sleep over at a grandparents house/family...we just don't have anyone here really besides my mom, and she's casually mentioned him staying, but he's never asked so never has and we've had no reason/occasion to leave them here with anyone..
Actually, we did try and leave them at my moms the night of my 30th, but she called at like 2 a.m. because Noah wasn't having anything to do with staying there, he was still 2 then, so DH went and got them...that was the first and only attempt.
You should definitely try having them stay at your mom's again now that they're both older. It would also probably be fun for them to each get to stay at her place on their own, without the other.
As you know, my girls have been staying overnight at my mom's house since they were really little. Madison has even had a couple of sleepovers at a friend's house already, and she has had no problems at all with it because she's so used to having sleepovers at grandma's.
Christian is definitely not too young for a sleepover.